What are plastics?

The word plastic came from the greek word plastikos meaning capable of being shaped or molded. Plastics are wide range of synthetic or semi-synthetic organic solids that are moldable.

What are plastics made of?

Plastics are made of small organic molecules containing carbon along with other substances.

Each small molecules is known as monomer, which is capable of joining with other monomers to form long molecule chains called polymers.

 Polyethylene-simplest polymer structure.*

Structure-to-function
The different properties of plastic came from the different molecular groups that are attached to the monomer units that in turn customizes the property of the polymers.

 Fillers improves the production of plastics. Stabilizing additives like fire retardants lower the flammability of the plastic, Plasticizer , which are oily compounds, are blended to improve the rheology. Colorants adds dcor and variety. To

Classification
Chemical Structure of polymer backbone -acrylics, polyester, silicone, halogenated plastics Chemical process used in synthesis -condensation, polyaddition and crosslinking

Production of plastics
Gathering of raw materials Synthesis of polymer Inclusion of additives Shaping and finishing

Raw materials
Primary petrochemicals -ethylene, propylene, benzene, etc. Intermediate chemicals -ethylbenzene Monomer -styrene

Synthesis of polymer
Monomer units undergo polymerization. Two basic polymerization methods are addition and condensation. Can occur in gaseous, liquid and occasionally solid phase.

Inclusion of additives
Catalyst enhances polymerization. -common catalyst???? Additives for customizing the plastics properties are added. Finally, the plastics are shaped and finished.

Steel Strength Plastics

In October 2007, University of Michigan researchers developed a nanoinfused polymer that is as strong as steel as thin as plastic wrap

 Robotic machine Resulting plastic from the as thin as plastic wrap

experiment

Steel Strength Plastics

Prof. Moshe Kol of TAUs School of Chemistry developed a superstrength polypropylene Salalen titanium complex in highly isospecific polymerization of propylene and 1-hexene

Catalyst is the answer

Since almost every plastic use the same building block (polymer) the key in developing a better plastic is the catalyst used in polymerization.

Salen and Salan ligand

Salens are class of organic compunds used as ligands in coordination chemistry and homogeneous catalyst. Salen derived from the simplest sample, N,Nbis(salicylidene)ethylenediamine

Salen and Salan ligand

Condensation of ethylenediamine and salicylicaldehyde Salan ligands are saturated at the nitrogen, are more amines rather than imines

Salalen ligand
Intermediate between salans and salens. Complexes tend to be rigid and more electron rich at the metal center than the corresponding salen complexes.

Salalen ligand
Salalen complexes are made by reacting the diprotic pro-ligand with metal precursors containing bases or metal halides.

3,5-dibromosalicylicaldehyde N-Methylethylenediamine Salicylaldehyde S-(2)-Pyrrolindinemethanamine.2HCl Triethylamine 3-Adamantyl-2-hydroxy-5methylbenzaldehyde

Experiment

Synthesis of metal complex

Each ligand precursor (1-5) were added with 1 mL of ether and added dropwise to a solution of Ti(OiPr)4

Solution was stirred for 2 h, the solvent removed under vacuum, and the resulting yellow solid was washed with pentane.

Synthesis of metal complex

Finally 1 mL cold toluene were added dropwise, solvent removed in vacuum, forming brown precipitates.

Ti dark gray Na blue O red I - purple

Synthesis of metal complex

Metal-ligand complex Final yield result Lig1TiBn2 Lig2TiBn2 53 mg (95%) 61 mg (86%)

Lig3TiBn2
Lig4TiBn2

110 mg (100%)
105 mg(95%)

Lig5TiBn2

71 mg(96%)

Synthesis of polymer
Two co-catalyst used: Tris(pentafluorophenyl)borane - co-catalyst in metallocene-based industrial processes for the homogeneous polymerization of olefins. Methylalumoxane (MAO) most wellknown catalyst in olefin-polymerization

Structure of tris(pentafluorophenyl)borane

Proposed structure of MAO

Polymerization with B(C6F5)3

B(C6F5)3 was dissolved in 1 mL 1hexene and then added to a solution of Lig1-5TiBn2 in 4 mL 1-hexene. Resulting mixture was stirred for 2-4 h, and yielded poly(1-hexene) as an orange gum.

Polymerization with MAO

Lig1-5TiBn2 was dissolved in 1 mL 1hexene and added to a solution of MAO (50-500 eq) in 4 ml 1-hexene. The mixture was stirred until viscous then treated with acidified methanol solution and extracted with chloroform.

Polymerization of propylene with MAO

Lig1-5TiBn2 and 500 eq. of MAO were condensed with propylene in a stainless steel reactor for 13-14h in RT. Polymer solution were treated with acidified methanol and pet ether soln. Insoluble polymers were filtered and air dried.

Advantages
It does not easily decompose but it can instead be recycled. Products are chemically resistant, durable, easily shaped, thermally and electrically insulating.

Applications
Green manufacturing since durability of the plastics results in products that require less maintenance and much longer life.

Applications
New and improved plastics can replace steel parts in automobiles, so cars would be more lighter and consume less fuel.

Applications
Can be used to replaced water pipes made of steel and cement that are susceptible to water leakage.

References
http://Steel-strength.plastics/Durable.plastic..replace.metals.htm http://Making.Plastic.as.Strong.as.Stee/Scientific.American.htm http://Steel-strength.plastics.--.and.green,.too!.(6.15.2012).htm http://Ang.mga.resulta.ng.Google.para..sa.http://ars.elscdn.com.content.image.1-s2.0-S0378775310000856-gr1.jpg.htm http://Angewandte.Chemie.International.Edition-Volume.50,.Issue.15..April.4,.2011-Wiley.Online.Library.htm http://Journal.of.Molecular.Catalysis.A/Chemical/Structure.and.perform ance.of.the.solid.methylalumoxane.at.temperatures//E293250.C2.//Exp erimental.and.DFT.calculation.study.htm http://www.cleanproduction.org/manufactufing/pdf.php Konstantin Press, Ad Cohen, Israel Goldberg, Vincenzo Venditto, Mina Mazzeo, Moshe Kol. Salalen Titanium Complexes in the Highly Isospecific Polymerization of 1-Hexene and Propylene. Angewandte Chemie International Edition, 2011; 50 (15): 3529 DOI:10.1002/anie.201007678

Thank you!